Triphenylphosphine → HCID 16731668, compound

HRID 2307817Notes

Reaction equation

HRID 2307817 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:38][C:39](=[O:53])[NH:40][C@@H:41]([CH2:51]O)[CH2:42][O:43][C:44]1[CH:45]=[N:46][CH:47]=[C:48]([Br:50])[CH:49]=1)([CH3:37])([CH3:36])[CH3:35]>C1COCC1.CC#N.C1COCC1>[C:34]([O:38][C:39]([N:40]1[CH2:51][C@H:41]1[CH2:42][O:43][C:44]1[CH:45]=[N:46][CH:47]=[C:48]([Br:50])[CH:49]=1)=[O:53])([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 16731667HCID 16731667, compound

Product 1

HCID 16731668HCID 16731668, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22177404Acetonitrile tetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

Ph3P (1.13 g, 4.32 mmol) was dissolved in 9:1 THF/CH3CN (30 mL) and cooled to 4° C. with an ice/water bath. DIAD (850 μL, 4.32 mmol) was added slowly. After stirring 15 min, a solution of Example 273B (1.0 g, 2.88 mmol) in THF (4 mL) was added slowly. The solution was allowed to warm to rt and stirred for over night. The solution was concentrated and the residual oil was purified by flash chromatography (20-40% EtOAc in hexane) to give the desired product (1.0 g, 75%). MS (DCI) m/z 329, 331 (M+1)+.

Workup

  1. temperatureto warm to rt
  2. stirringstirred for over night
  3. concentrationThe solution was concentrated
  4. customthe residual oil was purified by flash chromatography (20-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-3d8285eab7654cc5827d0db26b683d5d
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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